Advertising Technology

First Round Capital

Check: Not applicable to his current role: First Round states that Chris has made no new investments since becoming a Board Partner in 2019. Historical round or check data should not be used to imply current investment authority.

Chris is now a portfolio-support and board partner rather than an active new-investment partner. His historical investing centered on advertising and marketing technology, social and mobile products, ecommerce and travel, connected devices, and gaming. The through-line in his current work is relationship-driven company building: connecting founders to people, resources, partners, and advice that can help them go the distance.

Union Square Ventures (USV)

Check: USV states that the firm writes $1 million to $30 million checks from the earliest stages onward. It does not publish Brad's personal range or authority; investments are discussed by the full partnership and decided collectively without a vote.

Brad's published investing work centers on preserving the internet's permissionless, generative character. He has backed open communications and data infrastructure, decentralized protocols with incentive-aligned funding models, community fiber networks that challenge access monopolies, and data-driven media platforms entering a market transition. The common thread is reducing gatekeeper control while creating networks whose users, developers, and communities share in expanding value.

Craft Ventures

Check: No personal check-size range is published. Craft invests from angel/seed through venture and growth; amounts in Bryan's investment announcements are total company rounds, not his personal or standard Craft checks.

Bryan applies a growth, revenue, and marketplace lens shaped by building Reddit's New York revenue organization and Twitter's startup advertising business. His investments favor products that remove expensive operational friction, demonstrate clear founder-market fit, delight customers enough to produce strong advocacy, and can use software, AI, services, or community-led distribution to create a meaningful performance advantage.

First Round Capital

Check: No current personal check range or new-investment authority is published. Richard's official Board Partner role focuses on coaching existing First Round companies; firm-wide check ranges should not be attributed to him personally.

Richard applies experience from building startups and running global revenue organizations to help First Round companies navigate go-to-market. His stated scope spans GTM strategy, customer segmentation, product strategy, team building, and operating at scale. His value is less a sector prediction than pattern recognition across zero-to-one, the messy middle, and hypergrowth.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Marco Caradonna invests through BlackSheep Ventures's published strategy: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Marcello Giordani invests through BlackSheep Ventures's published strategy: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Antonio Dettoli supports BlackSheep Ventures, whose published strategy is: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Brian O'Kelly supports BlackSheep Ventures, whose published strategy is: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Gustav Mellentin supports BlackSheep Ventures, whose published strategy is: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

Y Combinator

Check: YC's live standard deal is $500K for every accepted company: $125K on a post-money SAFE for 7% plus $375K on an uncapped MFN SAFE, with a future participation right. This is YC's program deal, not Brad's personal check, and founders should read the current official terms before applying.

Brad helps very early founders move from idea to a launched product users want, then build the fundraising, hiring and customer-development habits needed to survive. His Perfect Audience background and YC teaching focus point to practical evaluation of distribution, ideal customer, conversion to paid use, capital efficiency and whether a founding team learns quickly enough to find product-market fit.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Umberto Bottesini invests through BlackSheep Ventures's published strategy: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Check: BlackSheep Ventures does not publish one standard current check-size range on its official site.

Sandro Moretti invests through BlackSheep Ventures's published strategy: Back European AI-native founders applying domain-specific software and automation to complex markets and industrial sectors.

BlackSheep Ventures

Milan, Italy